Microsoft is adding Cortana to Skype, but to make use of the intelligent assistant you’ll have to let her listen in on your conversations. Those who are happy to do so will get the benefit of her knowledge, as she offers up useful information related to what you and your contacts are talking about.

Cortana Fills That Friend-Shaped Hole

The ability to eavesdrop is exactly what Microsoft is now offering. In a Skype Blog post, the Skype Team has announced that Cortana can now be a part of your Skype chats. She’ll even be a contact in her own right, so you can have one-on-one conversations with her when you’re bored or lonely.

Beyond that, Cortana will offer “in-context assistance” within your conversations with other people. This means recommending restaurants, offering up movie reviews, and suggesting smart replies. She can also help you schedule events or set up reminders. Like all the best stalkers.

Cortana will automatically be added as a contact in your address book and on your contact screen. To enable her to get involved in other chats just tap on her name to start a conversation, and then, when asked for permission, allow her access to your location and IM conversations. If you dare.

The fact that this is opt-in rather than opt-out is good, and should allay most privacy concerns. However, people will want to take advantage of Cortana’s new-found skill. And doing that means letting Cortana be that creepy person on the bus listening to what everyone else around is saying.

Will you be adding Cortana to Skype? If so, do the privacy implications not bother you? If not, why not? Do you accept that getting the most out of technology means giving up our privacy? How do you feel about digital assistants like Cortana and Siri? The comments are open below!